Well I spoke to a few dealers and they all seem to confirm that even the SS rudder ports need greasing and so that's what I did. I replaced the grease fitting and greased it until it shot out the bottom of the hull. Two results. Super smooth steering and no water leak. Since the grease fitting is stripped my OCD requires me to pull the whole rudder port off at a later date and replace but this job looks fairly straight forward. Am I correct in assuming that 3M 4000 fast cure sealant is the one to use?